Dichloromethane → HCID 20192963, compound

HRID 2118724Notes

Reaction equation

HRID 2118724 reaction equation
ClCC[CH2:4][CH2:5][CH:6]([S:14][CH:15]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[N:22]=1)CCCCCl)C1C=CC=C(C)N=1.ClC1C=CC=C(C(OO)=[O:36])C=1.[CH2:39]([Cl:41])Cl>>[Cl:41][CH2:39][CH2:4][CH2:5][CH2:6][S:14]([CH2:15][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[N:22]=1)=[O:36]

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 70297m-Chloroperbenzoic acidHCID 70431222HCID 70431222, compound

Product 1

HCID 20192963HCID 20192963, compound

Conditions

Temperature
20 °C

Procedure

To a solution of 4-chlorobutyl(6-methyl-2-pyridyl)methyl sulphide (9.2 g) in methylene chloride (140 cc), an 82.5% strength solution of meta-chloroperbenzoic acid (8.2 g) in methylene chloride (90 cc) is added dropwise in the course of 1 hour 30 minutes at a temperature in the region of 15° C. The mixture is stirred for 16 hours at a temperature in the region of 20° C. and then poured into neutral silica gel (225 g; 0.063-0.200 mm) contained in a column 4.3 cm in diameter. The column is eluted successively with methylene chloride (2.5 liters), a mixture (500 cc) of methylene chloride and ethyl acetate (50:50 by volume), ethyl acetate (500 cc) and a mixture (1.25 liters) of ethyl acetate and methanol (90:10 by volume), collecting 250-cc fractions. Fractions 15 to 19 are combined and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 50° C. 2-[(4-Chlorobutyl)sulphinylmethyl]-6-methylpyridine (8.8 g) is thereby obtained in the form of a yellow oil, and this is used without further purification in the subsequent syntheses.

Workup

  1. additionpoured into neutral silica gel (225 g; 0.063-0.200 mm)
  2. washThe column is eluted successively with methylene chloride (2.5 liters)
  3. customa mixture (500 cc) of methylene chloride and ethyl acetate (50:50 by volume), ethyl acetate (500 cc) and a mixture (1.25 liters) of ethyl acetate and methanol (90:10 by volume), collecting 250-cc fractions
  4. concentrationconcentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 50° C

Sources & evidence

ORD record
ord-81bb9cf897aa47798fdab23290aa6b7f
Source dataset
uspto-grants-1987_07
Patent number
US04680303

Reaction notes

Loading…